APPENDIX I'henylhydra/ones <".re not formed, .as phcnylfiydrazine acts as a reducing ;igent and produces quinol.^ The constitution of quinhydrohe. tfep intermediate formed by the reduction of quinoneS,^ <&\da&jq<ft», oT"" represented by the formula, ^^^^IJ. ~ ^.«*- /)----C(OII) " 4\ nc\Jui For the formation of dimcthylquinone, sec p. 251. Pkl<: PA RATION 86. Benzyl Chloride.--The action of chlorine on boiling toluene is quite distinct from the action which occurs in the rold or in presence of a u halogen carrier " (see pp. 252, 271). In the present instance substitution takes place in the side- chaiu. It is a curious fact, however, that: clllorinc produced by elect rolysis \\\ presence of boiling toluene mainly enters the nucleus. P.y prolonged action all three hydrogen atoms of the side-chain may be replaced, and the following compounds obtained: Ct.lI,(ClU;i Ben/yl Chloride. (',';! r,CI ICK, iJciixal Chloride. C,jII..(CCl., ncny.otridiloride. Hydrocarbons containing the halogen in the side-chain may be L'.cncrany, though not. invariably distinguished, by their irritating action on the eyes and mucous membrane of the nose, from those in which the halogen is present in the nucleus. Moreover, the halogen in the side-chain is much more readily substituted or removed than when it occurs in the nucleus. In this respect the above compounds resemble the members of the aliphatic series (alkyl and alkylene halides). Benzyl chloride is decomposed by water, ammonia, and potassium cyanide, forming ben/yl alcohol, ben/yl cyanide, and benzylamine. c,;ii,ciu:i ! ju) - (Viir,cii,OTi -i- nci c(iH,cn,ci i KCN .- (;,,nBciiaCN + KCL Jlcn/yl cyatiidf, (VJI^'H-/1! I 2NII:,.....C.-HnCH.jN'IIo ) NH4C1.